Ep. 99 – Leading and Scaling Revenue Organizations When the Old Playbook Is Obsolete - Part 1
Ep. 99 – Leading and Scaling Revenue Organizations When the Old Playbook Is Obsolete - Part 1  
Podcast: Selling the Cloud
Published On: Tue Oct 28 2025
Description: In this episode of Selling the Cloud, we’re joined by Neil Graham, Chief Revenue Officer at Disqo and a seasoned revenue leader whose career spans Salesforce, Siebel, Jive, and Telem. Neil shares a ground-level view of what it takes to lead, scale, and modernize revenue organizations in an era where traditional sales playbooks are no longer enough.From breaking out of funnel-stage rigidity to building flat organizations that prioritize curiosity, Neil walks through the changes CROs must embrace to stay ahead. He also shares how Disqo is rethinking GTM structure and leveraging AI to drive personalization, speed, and operational clarity; without drowning in tools.What You’ll LearnWhy the Playbook is Obsolete: What Neil really means when he says the old models no longer work, and what replaces them.Lightweight Rigor at Scale: How to build process and alignment without slowing teams down.From Bottoms-Up to Top-Down TAM: How Disqo blends relationship selling with TAM-led targeting for scale.Curiosity as Culture: Why curiosity is a non-negotiable leadership trait in flat, fast-moving GTM orgs.Leading Through Change: How to coach teams to self-govern, move fast, and stay mission-aligned in a no-layer org model.Key TopicsBuilding sales organizations without bureaucracy or bloatAligning marketing, sales, and success teams around business outcomesUsing AI to power real-time customer insight and hyper-relevant outboundFlattening GTM structures for speed, ownership, and clarityCreating cultures where experimentation and impact are rewardedGuest Spotlight: Neil GrahamNeil Graham is the Chief Revenue Officer at Disqo and a proven sales leader with decades of experience scaling GTM organizations from Series A to post-IPO. Known for his ability to bring structure without red tape, Neil has helped some of the most recognized B2B SaaS names balance scale with agility in high-growth phases.Resources & MentionsCompany: DisqoFramework: DSF (Disqo Success Framework)Sales Tools: Gong, Clay, ChatGPTBooks & Influence: MedPick methodology, Salesforce early days, AI-led sales enablement🎧 Listen now on Apple Podcasts, Spotify, or wherever you get your podcasts.Mark Petruzzi (00:33)Welcome to today's episode of Selling the Cloud Podcast. We're excited today to welcome Neil Graham, Chief Revenue Officer of Disco. Neil is a proven revenue leader who has helped scale organizations at Salesforce, Siebel, Jive, Telem, and now Disco, the best name of them all. At Disco, Neil leads a go-to-market organization of about 45 inside a nearly 300-person company.KK Anderson (00:33)Thank you.Mark Petruzzi (01:00)His career spans taking companies public, guiding series A to series F growth, and balancing early stage venture backed and private equity operating models. Today, Neil will share what it looks like to lead and scale revenue organizations when the old playbook is obsolete, which pretty much is all the time nowadays. Covering agility,operational discipline, and why CROs must embrace a new approach to building revenue in 25 and beyond. Here are the four themes we'll explore. First, when the old playbook is obsolete. So when these old legacy models no longer fit, no longer work, how do leaders adapt? Scaling from 10 to 100 million, that sweet spot, especially in the SaaS and ISV world.And then, the concept of lightweight operational rigor, like how to combine a sleeves rolled up selling model with really good process and tools, but not too many process and tools slow How flat orgs need to be structured and how they work and how that really puts more pressure and responsibility on the CRO.and also sprinkling AI into the go-to-market mix. How Neil is experimenting with AI to augment productivity and rethink traditional roles. Neil, thank you so much for joining us. Welcome to Selling the Cloud.Neil (02:26)Thank you, Mark. Appreciate it. Thanks for having me.Mark Petruzzi (02:30)Happy to have you here. All right, topic one, when the old playbook is obsolete. So, Neil, I've heard you say, don't even know what the playbook is right now. It's all getting disrupted. Tell us a little bit about what you meant by that.Neil (02:43)thanks for the introduction. That was great. look, privileged to be at a lot of great companies through the years and hopefully caught on to a little infrastructure and kind of prioritization through the years in terms of how I approach things. we're in a really unique age today.the traditional playbooks from the last, I'd say 20, 25 years in a way, are going out the window in a way they're still there. And I think if you think about what's happening with AI and with how that impacts operational structures, go to market strategies, people and process skills.And overall playbooks, it's like you really have to kind of reconsider the way you're operating at every step of the way yet continue to operate and make sure that you put one foot in front of the other and execute. And so what does that look like? we've spent a lot of time. I think about the back in the days at Oracle in the early days and then at Salesforce, where we really scaled some organizations from small to large.the playbooks that we created around, marketing and sales and customer success became kind of a standard. And it's like, if you think about the processes from lead development, MQLs to SQLs to, early stage pipeline and the sales process from stage one to being selected at stage four or five and getting into a negotiation, the process of value selling along the way where you identify.the customer's business issues and challenges, you map your solution to that. You think about trying to position how you're unique against the competition or the status quo and quantify that, that value and articulate that really well to the client. A lot of that was put on our people and we would train and enable around these processes and these plays, try to roll out frameworks like, every part of the sales process, dissecting it.providing people visibility and information into what it takes to be successful, whether it comes to discovery, whether it comes to running a great demo, whether it comes to positioning the differentiated value prop, whether it comes to building the business case of the impact that you're going to make at the organization in terms of driving business outputs, whether it comes to scoping and professionally delivering a plan to make the customer successful, whether it comes to the negotiation, the objection handling, the competitive intel.All that stuff's still there. And our customer facing people and processes need to execute flawlessly on that. At the end of the day, it's just that the information is so readily available and we'll talk more about it later with AI have to do everything that I just said, but it's so flat in terms of being able to access that information, position that information on the fly.and make it part of your cadence that some of the traditional models of the playbooks and the enablement plans and the objection handling frameworks and all that kind of stuff literally go out the window and they become kind of almost in the moment. So I don't like at the end of the day, I think the old playbook being obsolete, I don't know. I think from my point of view, customer value still wins,the modern model starts with the customer's business case, knowing their business issues and challenges, understanding the pressures and constraints they have, and your people being able to flush that out and have that information at their fingertips when they come into a conversation. Then being able to articulate how the solution that they bring to market is differentiated and tie that differentiation to the measurable outcomes.It's just doing it in a more productive and higher impact and flatter and faster way. But every interaction that you have should clarify, how you come back to the business issue and challenge the customer has. So I think second, the AI tech that's out there puts these answers within reach and, we're able to have this information quicker and faster than ever before. And then I think third, just creating a culture and sort of a overall.go-to-market system that is rooted in curiosity. So your people and your processes continue to evolve quicker and faster than the competition is really important for every company.KK Anderson (06:30)I echo everything you said, Neil. this morning, as a matter of fact, I pulled out my phone and I wrote it in my notes thought exactly what you just said. The activities, what's changed now is that the activities aren't the work. Going into CRM and working in CRM, that is what's obsolete. Right? You can't do the same things every day and expect to have a differentiatedcustomer focused, customer obsessed approach, right? it's all about leveraging all of this super intelligence, leveraging AI, what's at our fingertips to do the hard. And so sales, in my view, is going back to what it was originally, the beginning of the sales profession, right? Where it was all about solving problems asking great questions and getting to know people and relationships.And then we had all of these years of playbooks here's what you do, here's what you say, here's how you handle this objection, here's how you position this, here's how you differentiate this. And it's almost now, like the second something gets turned into a PDF, it's no longer relevant, right? And so it is interesting. All of this is allowing sellers to do the hard things, which is if you go a day or a week,God forbid, and you don't feel that anxiety of what am I gonna say on this call or how am I gonna approach that person, then you're not doing the hard things. Ticking off tasks is old school. That's the old playbook, right? Anyhow, so as you think about this kind of seismic shift that's happening, what are the principles that are guiding you as you lead today? If you're going back to basics,back to you were just talking about, like what are those principles? Like how do you lead through this kind of a change?Neil (08:04)Yeah, look, first of all, think, it goes a little bit to the second kind of area of discussion. It's sort of how do you create this lightweight operational rigor, especially as you scale companies I've kind of been at a few companies now that are series A, series B. there's a disruptive technology that's solving for a problem uniquely in the market. Doing it, it's a better mouse trapthan what was there before. And because of this unique model, the unique data set, the cloud, whatever it is, it's able to solve the problem in a more effective, more efficient, more holistic, better quality way. The company I'm at right now is disrupting the marketing media effectiveness measurement market, the old stodgy providers that are out there that weren't as innovative and disruptive.We're disrupting that. I'm entering into a company, I've been here about a year and a half, where had, a better mousetrap than the competition, that a company could build on their own. Companies want a partner, they don't want to kind of be in the core competency of doing what we do. so we've been taking share from the competition.in the early days as we built the product five, six years ago and started to take it to market, we hired some good people from the competitors and knew the space and they brought their book of business and their relationships and it was a lot of hard work. Don't get me wrong, but at the end of the day, we were able to take share where we had relationships and where we had knowledge and sort of the bottoms up, right? And now we're moving more towards what I'd say is understanding the total addressable market.aligning our skills and our people and our organization around that, picking our bets on where is the biggest total addressable market, what can we take on right now as we scale and grow and we get past 50 and 100 and 150 million, aligning our skills and resources, training and enabling, getting the right people, hiring the right people, all that kind of stuff to go take the market more from the top down. Having that bottoms up, but also that top down where...We know this is the right place for us to aim the arrow and shoot. And we're going to put a lot of emphasis behind where we shoot and make it really impactful, improve our win rates, execute more flawlessly from marketing to sales to success and do a great job serving that market. So as we look at doing that and things are at the same time getting disrupted by AI, I've kind of run this play before where you're taking a company from 10, 20, 30 million to hundreds.and have the playbook and kind of like know the motion, right? You build in some process, you bring in world-class tools, you align your people and your skills to the market opportunity, you help limit the distractions on stuff that's not within that market opportunity that's the biggest bang for the buck. However, you still have to be nimble, you still have to kind of pay attention and pivot at the same time.And so there's a lot of art and science to rolling out lightweight process and tools and enablement and skills, yet at the same time, not over engineering it so we can go execute and we don't get in our own way and we don't have a lot of bureaucracy and there's not a lot of layers. And I think we've done that really nicely here. It's like I kind of came into an organization where we had a marketing team and there was a bunch of different pockets ofweird reporting structure. And we quickly fixed that where it's me to my heads of marketing versus like in demand gen versus product marketing versus PR and comm and then they have teams, right? And then on the sales side, we did the same thing. We kind of had a one size fit all motion for the salespeople and they were kind of going after the market based on what they all knew. We layered in where do we need to be and what skillsand tools do we need to have in order to go attack that market? Let's bifurcate the sales team because we saw two plays going on in the market. And we did that. We aligned the right people with the right opportunity. We hired the right people coming in to grow into these two opportunities. And we've rolled out playbooks and processes and competitive packages and, objection handling frameworks and all that kind of stuff for all the people that are in these two swim lanes in terms of how we go to market. What's been really cool in the last12 months is we've embraced AI to just do all that bigger, better and bolder. Right. And so, answering your question, I think first, leaders need to get out there and be in the market, especially at this size of a company. can't, more so than ever. It's, like, you have to be in the field. You have to be with your customers. You have to be with your teams. If you're not spending 50, 60, 70, 80 % of your time.even as the CRO is the operational leader, executive part of the executive committee, all that kind of stuff. If you're not out there in front of the market, then something's wrong, right? So that's number one. Number two, just building this culture of genuine curiosity, I think is critical. You have to hire then promote and exit people based on curiosity or a lack thereof.And that's in everything you do. It's if people aren't asking questions, if they're not genuinely curious in front of the customer, in front of their own internal teams, if they're not innovating and trying new things, and if they're continuing to be focused on delivering the results, right? Like we have OKRs here. We call it DSF, the Disco Success Framework. My marketing team knows exactly what's expected out of them when it comes to the specificoverarching business goals, the key metrics to achieve those goals on a weekly, monthly, quarterly basis, and the initiatives that they have to go solve, to go generate those key metrics that they continue to evolve around. We're kind of continuing to tweak our initiatives every month, every quarter, to make sure that we're hitting the actual metrics in alignment with our objectives. And if you don't have people not only being curious and being innovative, but also keeping their eye onHey, is this an alignment with the objective and the key result that I'm trying to drive? And if it's not, what the hell am I doing? Let me stop doing that, right? And allowing people to be informed around that, have the information be very clear so they can almost self-govern because as you create a flat organization, there's a lot of greatness with that, but there's a lot of challenges that come with that as well. And you have to allow people the power to kind of understand, does this map back to the key objective and...desired outcome that I'm working on. if it doesn't call an audible, let's get the hell out of here and let's stop doing this. Right.Mark Petruzzi (14:07)Well, Neil, you have me thinking and wishing this was an investor presentation rather than a podcast. And what I mean by that is we, get to a fair amount of opportunities to hear CROs like yourself when they're looking for funding and, get to get excited about that or not excited about that. And you actually made me put together a thought that has happened in the back of my mind many times, butnot as clear as today. And that is when we're doing this podcast and a CRO or a CMO gets on and, or a CEO gets on, they start talking about their approach. And I start to just think exactly that of, this should be an investor presentation because I, want a piece. So that's very impressive. As you know, I hear these things and we have podcasts every week as well. So I love the way you, positioned all that and you went,radiant to this direction, but I'd like to have you tap a little bit and go a little deeper.Neil (15:03)it kind ofa little bit of the, how do you build in this operational rigor, but also like, how do you do it in a flat world? So, I mean, feel free to drill in there because it was kind of two of those.Mark Petruzzi (15:14)Yeah, nowthat's great. And I also like, you described how these some CROs are clinging to these old cadences and funnel metrics and SDR handoffs and the whole process of lead generation. What do you feel are broken about these models and a little bit on how do you fix them?Neil (15:31)I don't know if it's broken. I mean, look, don't get me wrong. we still have operational metrics that we look to kind of the leading indicators on a weekly and bi weekly and monthly and quarterly cadence. And still one of the objectives is an objective around, MQL and lead creation, right, that my marketing team owns andSQL and down funnel lead, qualification that the BDR team owns and SAO generation, which is our stage one opportunity that the BDRs and the AEs and the CS team own in terms of creating net new pipeline. And we have a certain amount of pipeline that we got to create every week, every month, every quarter. And, we're trying to be in front of it with key initiatives that we're rolling out to improve our outbound motion.And we're looking at Salesforce dashboards and summarizing all this stuff up.just take the sales team, for example. We've got about 20 sellers and I've got three SVPs. And so our sellers are director and VP level, our SVPs are managerial level and they report to me. And so we flattened it those three layers. In marketing, it's three layers across the whole organization.on our success and delivery teams and our product teams and our engineering teams, we've gotten it down to three layers. I think that's really helped us as a business. Our CEO drove that and...made it a mandate and not everybody kind of understood the why. And we did a lot on our all hands calls and our internal communications to help people understand the why behind all this. And over a period of about a month, month and a half, we got the company that flat. And the goal was to get faster information flow and get quicker, better decisions and have more experimentation and fail faster and succeed faster, right? And just have.higher organizational ownership and impact, have impact be visible, versus lost in silos. And if you can really then build your, internal compensation and promotion and recognition system, which we do a lot there, we do stuff on a quarterly, biannual and annual basis around those subjects. If you can build it around impact.And make it impact based in alignment with your goals and objectives back to your OKRs and promote the people that are having high impact. Those are going to be the people that are the most curious. Those are going to be the people that are experimenting the most. And, if you do this the right way, you'll start to set those examples. And pretty quickly within about a year and year and a half, we've weeded out a lot of people that aren't curious. we've kind of weeded out people that aren't trying to make an impact.Now the challenges with that is when you have that flat of an organization, it can really blur decision kind of ownership and there can be competing initiatives and there can be some accountability gaps and it can overload some of your managers and your leaders. I'll give you an example. It's like my CEO and I are very tight at the hip on working with the marketing team andThere can be times where my CEO will grab people that roll into me and send them in a particular direction. And it's like, he and I have to be really well aligned on what are we trying to accomplish here? What are the goals and objectives of the company? And let's make sure that we're pushing people towards the same outcome, because if there's any competing interests, it can get confusing for our employees.And so just the communication and the collaboration and the work that we do, have at this company, we've got about two hours set aside every week for SLT alignment. that for the executive team to meet, to go through all the key initiatives and strategies, everything from people to process, to tools that we're using, to the outcomes and the initiatives that we have, and making sure that we're all in alignment.in this flat culture, we get everybody kind of pointed in the right direction. So hopefully that helped a little bit, it can create an opportunity, but there also can be a lot of challenges with it as well.KK Anderson (18:57)You know.Really, really insightful, Neil. Thank you for that.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.